Join Our Team

General Manager

Full Time • Brewster, MA • (Hybrid Cape Cod-based) 

About the Role

Nauset Rental is looking for a General Manager to run the day-to-day — lead the team, own our processes, and drive execution so we can grow. 

This is a leadership role with real authority. You’ll run our team, oversee owner relationships and escalations, install our processes (AI at the forefront), and make sure the business engines are humming. If you want to make a big impact by running the show, this is the seat. 

Our office is in Brewster. Schedules shift in-season with a degree of weekend and holiday availability is expected during the summer. This is a leadership role with significant responsibility and autonomy. While core working days will be scheduled, this position requires flexibility and availability for urgent operational matters as they arise. You'll have the freedom to manage your time effectively while ensuring seamless operations. 

Where We're Going

We’re targeting 40% year-over-year revenue growth, becoming the go-to vacation rental manager for high-end and luxury homes on Cape Cod. Once we own that niche, growth continues via other verticals and / or regions. 

AI is going to reshape this industry, and we plan to be at the forefront. We're using it to automate the not-fun parts of running a vacation rental company so the team can focus on the fun stuff — delighting guests, strong partnerships with homeowners, and delivering the high-touch service luxury demands. Deploying AI across our operation is a huge part of this seat.

What You’ll Do

• Lead the team: Directly managing and leading their professional growth, goals, performance and roles & responsibilities. 
• Build the org chart and make sure the right people are in place to execute on the broader strategy. Handle the recruitment engine and own a successful training and onboarding program. 
• Own our SOPs end-to-end: make sure they’re documented, improved, accessible, and consistently followed. 
• Oversee quality assurance in our reservation & guest services team, processes, and performance. 
• Be a primary contact for owner relationships and escalations. 
• Drive AI adoption across the team. As we build the AI strategy and tools, you build them into our SOPs, train the team, make sure adoption actually sticks, and keep tools tuned and improving as we learn. Surface new opportunities as you spot them.

What We’re Looking For

• 5+ years in a senior operating role at a small or mid-sized business — Director of Operations, GM, VP of Operations, or similar. You’ve reported to a founder, CEO, COO, or President before, and that relationship lasted. 
• A track record of leading and developing leaders, not just doers. You can name people you’ve grown into bigger seats 
• You’ve held a team together through a high-volume industry or season — summer resort, holiday-heavy retailer, hospitality operation, tax-season firm — and can talk specifically about how you kept quality high and burnout low. 
• An implementer, not a strategist. You take a clear plan and drive the team to execute it. Process discipline is your love language. 
• A builder. Comfortable walking into a small team with gaps and constructing the management layer yourself 
• Tech-fluent enough to lead a team through system migrations and AI rollouts without flinching. Real curiosity about AI as an operating tool. 
• Already on Cape Cod, or able to get yourself here year-round. 
• A GSD mindset. You take ownership, finish what you start, and don’t wait to be told twice 
• You're energized by building inside a small business with a clear path to major growth

Compensation & Benefits

• $80,000–$100,000 base salary, based on experience 
• Generous performance bonus, tied to outcomes we agree on annually. A substantial upside compensation component for someone who comes in for the long term, commits, and drives growth through strong leadership and clean implementation 
• 401(k) with 3% company match 
• Health / Wellness reimbursement 
• 3 weeks PTO. Paid holidays. 
• Hybrid schedule as seasonal schedules permit.

How to Apply

Email [email protected] with your résumé and a note about yourself. Tell us why this seat, why this business, why now. Bonus points for specifics: a time you took over a messy operation and made it hum, a process you built that outlasted your departure, or a team member you developed into a bigger seat. 

Business Development Associate

Full Time • Brewster, MA • (Hybrid Cape Cod based)

About the Role

Nauset Rental is building the leading vacation rental management company for high-end homes on Cape Cod, with a goal of 40% year-over-year growth. 

We’re looking for a driven, tech-forward business development professional to help turn premium homeowner prospects into new business. 

We already have the foundation: a prospect database, outreach playbook, proven templates, AI tools, revenue-projection models, and a strong homeowner offering. Your first job is to run that system consistently, keep prospects moving, and create qualified opportunities for our leadership team. 

You’ll use email, direct mail, referral outreach, and targeted calls to connect with homeowners and move strong prospects forward. You’ll also meet with homeowners, assess properties, prepare rental-income projections and proposals, and ensure every promising lead receives fast, professional follow-up. 

As you demonstrate strong judgment, sales ability, and follow-through, the role will grow. You’ll help further develop our AI-supported sales process while taking on more direct owner conversations, proposal strategy, negotiation, closing, and client relationship ownership.

What You’ll Do

• Run multi-touch outreach to high-value Cape Cod homeowner prospects. 
• Use AI tools for prospect research, personalized outreach, follow-up, and proposal preparation. 
• Respond quickly to interested prospects and call when a conversation will move the opportunity forward. 
• Qualify homeowners based on interest, fit, decision-making authority, and the home’s quality, availability, and revenue potential. 
• Prepare preliminary rental-income projections using our established model and market comps. 
• Book qualified, well-prepared owner conversations with the executive team. 
• Keep the CRM and pipeline accurate, current, and moving. 
• Reconnect with past prospects and nurture local referral relationships. 
• Visit homes and meet with homeowners to assess the property, understand their goals, and determine next steps. 
• Help improve and automate the sales process as you learn what works.

Who You Are

• An executor who likes a clear system, target, and measurable results. Motivated by earning more when your work produces more. 
• Comfortable using AI tools such as ChatGPT and Claude—or highly motivated to become proficient quickly—for research, drafting, and workflow improvement. 
• Organized and self-directed, and you keep your pipeline moving without constant oversight. 
• Resilient and consistent. Outbound work means hearing “no” and continuing forward. 
• A credible, trustworthy communicator who can speak confidently with homeowners by phone and in person. 
• A strong, natural writer who can turn a template or AI draft into a message that feels personal and specific. 
• Comfortable with numbers and can build a clean income projection in a spreadsheet or pro forma tool. 
• Experience in real estate, vacation rentals, hospitality, or property management is a plus.

Location

This is a hybrid role, not a fully remote position. We expect approximately two days per week in Brewster or elsewhere on Cape Cod, based on business needs. We are open to someone based locally or on the South Shore who can travel to the Cape consistently. Reliable transportation is required. Some weekend availability is required - prospective homeowners often want to meet while they are at their Cape homes. The schedule will flex accordingly.

Compensation & Growth

Business Development & Sales Representative

Flexible/Hybrid • Cape Cod, MA • Commission-Driven

About the Role

We’re looking for an ambitious, entrepreneurial salesperson who wants to build meaningful income by helping us grow. You’ll identify prospective homeowners, develop relationships, show them the value of professional vacation rental management, and guide opportunities through to signed agreements. 

This is not a role where you wait for leads to arrive. You’ll have an established company, prospect data, marketing resources, sales tools, and an experienced leadership team behind you—but your success will come from creating opportunities, following through, and closing business. 

Cape Cod real estate agents may find this especially appealing: your local knowledge and homeowner relationships can become another income opportunity without necessarily stepping away from your real estate business. But a license is not required. We welcome experienced sales professionals and ambitious people early in their sales careers who are ready to learn and produce results. 

We understand that building a sales pipeline takes time. Our intended compensation approach provides initial income support while you get established, paired with significant upside tied to the value and performance of the business you bring in.We already have the foundation: a prospect database, outreach playbook, proven templates, AI tools, revenue-projection models, and a strong homeowner offering. Your first job is to run that system consistently, keep prospects moving, and create qualified opportunities for our leadership team. 

What You’ll Do

• Generate opportunities. Prospect proactively through targeted outreach, networking, referrals, partnerships, and creative approaches to finding high-potential homeowners.
• Build homeowner relationships. Understand owners’ goals, earn trust, and explain how Nauset Rental can improve their rental experience and financial results.
• Own the sales process. Move opportunities from first contact through meetings, property assessments, proposals, follow-up, and signed agreements—with leadership support as you ramp up.
• Focus on quality. Identify homes with strong fit and long-term earning potential, not simply the highest number of new listings.
• Present the financial opportunity. Use our rental income models and market data to help homeowners understand potential results.
• Develop referral channels. Build productive relationships with real estate professionals, homeowners, and local business contacts.
• Manage your pipeline. Keep the CRM accurate, follow up consistently, and use AI and other tools to work efficiently and thoughtfully.
• Help us improve. Bring ideas, share lessons from the market, and help refine prospecting and conversion strategies.  

Who We're Looking For

• A genuine sales drive. You like reaching out, meeting people, developing opportunities, and earning based on results.
• Ownership and initiative. You manage your priorities and make things happen without needing a daily task list.
• Relationship skills. You communicate confidently and can establish credibility with homeowners making important financial decisions.
• Persistence and follow-through. You stay on top of prospects, handle rejection, and keep momentum through a longer sales cycle.
• Local knowledge or a relevant network. Cape Cod real estate experience or homeowner connections are a strong plus, though not mandatory.
• Commercial judgment. You care about property quality, long-term value, and the economics behind a deal.
• Comfort with technology. You’re willing to use a CRM, data, AI, and automation to support good sales habits.

Why Join Nauset Rental

• Earnings tied to impact. Our goal is to reward the expected value of the homes you bring into our portfolio, with additional opportunities based on actual performance after a rental season.
• Support while you ramp up. We intend to offer an initial draw to provide some income stability as you build your pipeline.
• Significant upside. We believe great salespeople should be rewarded for great results, with uncapped commission potential. 
• Flexibility. We focus on results rather than hours at a desk, while expecting consistent sales effort and accountability. 
• Tools and team behind you. Access prospecting resources, marketing support, AI-enabled workflows, and experienced leadership. 
• Room to grow. Join a locally led company targeting approximately 40% annual growth, with additional opportunities to be a part of the larger strategic road map if interested. 

Location & Expectations

This is a flexible, hybrid opportunity focused on Cape Cod, and South Shore applicants are also encouraged to apply. You must be able to meet homeowners in person, visit properties, and build local relationships. Some evening or weekend meetings may be necessary to accommodate owners. Much of the prospecting and follow-up can be done remotely.

We are results-driven rather than prescribing a fixed weekly schedule. Flexibility comes with clear expectations for consistent prospecting, responsiveness, pipeline management, and progress toward agreed new-business goals. The ramp-up period will include defined activity and performance milestones. 

Compensation & Earning Potential

Interested?

Send your resume to [email protected]. Tell us about your sales background, your connections to the Cape Cod market, and why this kind of opportunity appeals to you. We’re most interested in people who are ready to take initiative, build relationships, and turn effort into results.

Saturday Turnover Inspector

Part Time Seasonal • Brewster, MA 

About the Role

As a Turnover Inspector, you'll visit our properties each Saturday during the rental season to verify that homes have been cleaned and prepared to our standards before new guests arrive. This is a great opportunity for someone who is detail-oriented, self-motivated, and looking for consistent weekend work over the summer. You'll spend your Saturdays moving between beautiful Cape Cod properties — no two days look exactly the same. 

Additional hours outside of Saturdays may be available if that is of interest, but a commitment to Saturdays through the Summer are a requirement. Let us know if you’d like to work more than the Saturday shift!

What You’ll Do

• Perform quality checks on vacation rental properties – Document any issues in the stay management application using smartphone camera, our checklists, etc. 
• Stage finishing touches to ensure each home meets our presentation standards 
• Restock basic supplies as needed (e.g., paper goods, toiletries) 
• Complete various errands as needed 
•  Issue resolution - attention to detail and noticing a problem and working with guidance from the manager to resolve before incoming guests arrive. 

Requirements

• Available every Saturday from approximately 8 AM–4 PM 
• Committed to the core season: July and August (May through September availability is a plus) 
• Valid driver's license and reliable personal vehicle 
• Able to lift and carry up to 40 lbs comfortably 
• Strong attention to detail and ability to follow structured checklists 
• Comfortable using a smartphone for communication, checklists, and photo documentation 
• A team player attitude and willingness to roll up your sleeves and get the job done. 

Nice to Have

• Experience in hospitality, property management, cleaning, or a hands-on service role 
• Familiarity with the Lower or Outer Cape 
• A calm, solutions-oriented approach when issues arise

Compensation & Benefits

• $20-30/hour, commensurate with experience 
• End of season bonus 
• Mileage reimbursement 
• Paid training 

Work Location

This is a mobile, in-person role. You'll travel between properties primarily on the Lower and Outer Cape. Candidates must be able to commute reliably to the Brewster, MA area and surrounding towns. 

How to Apply

Email [email protected] with the subject line "Saturday Turnover Inspector – 2026." Please include: 

• Your availability for the 2026 season 
• A brief description of relevant experience 
• A resume or summary of your work background

Part Time Field Operations Specialist

Part Time Seasonal • Brewster, MA

About the Role

As a Part Time Field Operations Specialist, you'll be moving between properties, catching issues, and making sure our homes meet our standards between stays. Saturday turnover checks are a requirement, but your core commitment is in supporting our administrative team as boots on the ground, communicating clearly, moving quickly, and representing Nauset Rental at every property you visit.

What You’ll Do

• Perform quality checks on vacation rental properties – Document any issues in the stay management application using smartphone camera, our checklists, etc. 
• Stage finishing touches to ensure each home meets our presentation standards 
• Restock basic supplies as needed (e.g., paper goods, toiletries) 
• Complete field errands and handle last-minute logistics as they arise
•  Issue resolution - attention to detail and noticing a problem and working with guidance from the manager to resolve before incoming guests arrive. 
• Participate in the summer on-call rotation and adapt to shifting priorities during peak season 
• Fill in wherever the team needs you. No two days are the same.

Requirements

• Available every Saturday from approximately 8 AM–4 PM 
• Committed to the core season: July and August (May through September availability is a plus) 
• Valid driver's license and reliable personal vehicle 
• Able to lift and carry up to 40 lbs comfortably 
• Strong attention to detail
• Comfortable using a smartphone for communication, checklists, and photo documentation 
• A team player attitude and willingness to roll up your sleeves and get the job done. 

Nice to Have

• Experience in hospitality, property management, cleaning, or a hands-on service role 
• Familiarity with the Lower or Outer Cape 
• A calm, solutions-oriented approach when issues arise

Compensation & Benefits

• $20-30/hour, commensurate with experience 
• End of season bonus 
• Mileage reimbursement 
• Paid training 

Work Location

This is a mobile, in-person role. You'll travel between properties primarily on the Lower and Outer Cape. Candidates must be able to commute reliably to the Brewster, MA area and surrounding towns. 

How to Apply

Email [email protected] with the subject line "Part Time Field Operations Specialist – 2026." Please include: 

• Your availability for the 2026 season 
• A brief description of relevant experience 
• A resume or summary of your work background

Full Time Field Operations Specialist

Full Time Seasonal • Brewster, MA

About the Role

As a Full Time Field Operations Specialist, you'll split your time between the field and the office. Some days you are out moving between properties, catching issues, and making sure our homes are guest ready. Other days you are supporting the Guest Experience & Operations Specialists manage guest relationships, handle reservation inquiries, and share the administrative load.

This is a role for someone who thrives on variety; no two days look the same.

What You’ll Do

• Perform quality checks on vacation rental properties – Document any issues in the stay management application using smartphone camera, our checklists, etc. 
• Stage finishing touches to ensure each home meets our presentation standards 
• Restock basic supplies as needed (e.g., paper goods, toiletries) 
• Complete field errands and handle last-minute logistics as they arise
•  Issue resolution - attention to detail and noticing a problem and working with guidance from the manager to resolve before incoming guests arrive. 
• Participate in the summer on-call rotation and adapt to shifting priorities during peak season 
• Share administrative responsibilities with the Guest Experience & Operations Specialist — keeping property listings, internal systems, and guest records accurate and up to date
• Fill in wherever the team needs you.

Requirements

• Available every Saturday from approximately 8 AM–4 PM 
• Committed to the core season: July and August (May through September availability is a plus) 
• Valid driver's license and reliable personal vehicle 
• Able to lift and carry up to 40 lbs comfortably 
• Organized and detail-oriented — you notice what others miss and follow through without being chased
• Comfortable using a smartphone for communication, checklists, and photo documentation 
• A team player attitude and willingness to roll up your sleeves and get the job done. 

Nice to Have

• Experience in hospitality, property management, cleaning, or a hands-on service role 
• Familiarity with the Lower or Outer Cape 
• A calm, solutions-oriented approach when issues arise

Compensation & Benefits

• $20-30/hour, commensurate with experience 
• End of season bonus 
• Mileage reimbursement 
• Paid training 

Work Location

This is a mobile, in-person role. You'll travel between our office and properties primarily on the Lower and Outer Cape. Candidates must be able to commute reliably to the Brewster, MA area and surrounding towns. 

How to Apply

Email [email protected] with the subject line "Full Time Field Operations Specialist – 2026." Please include: 

• A brief description of relevant experience 
• A resume or summary of your work background